Design and synthesis of fluorescent 7-deazaadenosine nucleosides containing π-extended diarylacetylene motifs

TY - JOUR

T1 - Design and synthesis of fluorescent 7-deazaadenosine nucleosides containing π-extended diarylacetylene motifs

AU - De Ornellas, Sara

AU - Slattery, John M.

AU - Edkins, Robert M.

AU - Beeby, Andrew

AU - Baumann, Christoph G.

AU - Fairlamb, Ian J. S.

PY - 2015/1/7

Y1 - 2015/1/7

N2 - C-modified 7-deazaadenosines containing a diphenylacetylene moiety have been synthesised using cross-coupling approaches. The C-modified nucleosides exhibit remarkable fluorescence properties, including high quantum yields. Solvatochromic studies show a near linear correlation between the Stokes shift and solvent polarity which is indicative of intramolecular charge transfer. DFT calculations have allowed us to correlate the experimentally observed photophysical properties with the calculated HOMO-LUMO energy gaps within a series of real and model compounds. This journal is

AB - C-modified 7-deazaadenosines containing a diphenylacetylene moiety have been synthesised using cross-coupling approaches. The C-modified nucleosides exhibit remarkable fluorescence properties, including high quantum yields. Solvatochromic studies show a near linear correlation between the Stokes shift and solvent polarity which is indicative of intramolecular charge transfer. DFT calculations have allowed us to correlate the experimentally observed photophysical properties with the calculated HOMO-LUMO energy gaps within a series of real and model compounds. This journal is

UR - http://www.scopus.com/inward/record.url?scp=84915822635&partnerID=8YFLogxK

U2 - 10.1039/c4ob02081b

DO - 10.1039/c4ob02081b

M3 - Article

AN - SCOPUS:84915822635

SN - 1477-0520

VL - 13

SP - 68

EP - 72

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

IS - 1

ER -